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lumichrome
benzo(g)pteridine-2,4(1H,3H)-dione, 7,8-dimethyl- (9CI)

Supplier Sponsors

CAS Number: 1086-80-2Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:214-120-8
FDA UNII: 99U1UDJ2HM
Nikkaji Web:J9.483H
MDL:MFCD00005021
XlogP3-AA:1.10 (est)
Molecular Weight:242.23810000
Formula:C12 H10 N4 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Flash Point: 32.00 °F. TCC ( 0.00 °C. ) (est)
Soluble in:
 water, 674.2 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Riboflavin Impurity 2 (Lumichrome) > 95%
Odor: characteristic
Use: A derivative of Riboflavin.Riboflavin is a vitamin found in food and used as a dietary supplement. As a supplement it is used to prevent and treat riboflavin deficiency and prevent migraines.
Santa Cruz Biotechnology
For experimental / research use only.
Lumichrome
Sigma-Aldrich
For experimental / research use only.
Lumichrome
TCI AMERICA
For experimental / research use only.
7,8-Dimethylalloxazine >95.0%(HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for lumichrome usage levels up to:
 not for fragrance use.
 
Recommendation for lumichrome flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5326566
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
7,8-dimethyl-1H-benzo[g]pteridine-2,4-dione
Chemidplus:0001086802
 
References:
 7,8-dimethyl-1H-benzo[g]pteridine-2,4-dione
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5326566
Pubchem (sid):135028184
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
Golm Metabolome Database:Search
KEGG (GenomeNet):C01727
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2933.99.8210
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
 alloxazine, 7,8-dimethyl- (8CI)
 benzo(g)pteridine-2,4(1H,3H)-dione, 7,8-dimethyl-
 benzo(g)pteridine-2,4(1H,3H)-dione, 7,8-dimethyl- (9CI)
7,8-dimethyl alloxazine
7,8-dimethylalloxazine
7,8-dimethylbenzo(g)pteridine-2,4(1H,3H)-dione
7,8-dimethylbenzo[g]pteridine-2,4(1H,3H)-dione
 riboflavin lumichrome
 

Articles:

PubMed:In Vitro Antibacterial Phenolic Extracts from "Sugarbag" Pot-Honeys of Australian Stingless Bees (Tetragonula carbonaria).
PubMed:The B Vitamins Nicotinamide (B3) and Riboflavin (B2) Stimulate Metamorphosis in Larvae of the Deposit-Feeding Polychaete Capitella teleta: Implications for a Sensory Ligand-Gated Ion Channel.
PubMed:Differentiation of manuka honey from kanuka honey and from jelly bush honey using HS-SPME-GC/MS and UHPLC-PDA-MS/MS.
PubMed:IRMPD spectroscopy of metalated flavins: structure and bonding of M(q+)-lumichrome complexes (M(q+) = Li⁺-Cs⁺, Ag⁺, Mg²⁺).
PubMed:Probing protonation sites of isolated flavins using IR spectroscopy: from lumichrome to the cofactor flavin mononucleotide.
PubMed:Recognition of riboflavin and the capsular polysaccharide of Haemophilus influenzae type b by antibodies generated to the haptenic epitope D-ribitol.
PubMed:Alkaloids from the mangrove-derived actinomycete Jishengella endophytica 161111.
PubMed:A rapid fluorescence based method for the quantitative analysis of cell culture media photo-degradation.
PubMed:Cornflower (Centaurea cyanus L.) honey quality parameters: chromatographic fingerprints, chemical biomarkers, antioxidant capacity and others.
PubMed:A new isobenzofuranone from the mangrove endophytic fungus Penicillium sp. (ZH58).
PubMed:Competitive binding of abasic site-binding ligands and masking ligands to DNA duplexes for the analysis of single-base mutation.
PubMed:Floral markers of cornflower (Centaurea cyanus) honey and its peroxide antibacterial activity for an alternative treatment of digital dermatitis.
PubMed:Riboflavin and lumichrome in Dalmatian sage honey and other unifloral honeys determined by LC-DAD technique.
PubMed:Acid-base equilibriums of lumichrome and its 1-methyl, 3-methyl, and 1,3-dimethyl derivatives.
PubMed:Reverse structural genomics: an unusual flavin-binding site in a putative protease from Bacteroides thetaiotaomicron.
PubMed:The plant growth promoting substance, lumichrome, mimics starch, and ethylene-associated symbiotic responses in lotus and tomato roots.
PubMed:Molecular and functional characterization of riboflavin specific transport system in rat brain capillary endothelial cells.
PubMed:Classification and characterization of manuka honeys based on phenolic compounds and methylglyoxal.
PubMed:Antiprotozoal and antimicrobial compounds from the plant pathogen Septoria pistaciarum.
PubMed:Riboflavin's time-dependent degradation rate induced by ultraviolet A irradiation.
PubMed:The Arabidopsis phi class glutathione transferase AtGSTF2: binding and regulation by biologically active heterocyclic ligands.
PubMed:Metabolomics profiling of cell culture media leading to the identification of riboflavin photosensitized degradation of tryptophan causing slow growth in cell culture.
PubMed:Photosensitized amino acid degradation in the presence of riboflavin and its derivatives.
PubMed:Fluorescence solvatochromism in lumichrome and excited-state tautomerization: a combined experimental and DFT study.
PubMed:Stability and photodynamics of lumichrome structures in water at different pHs and in chemical and biological caging media.
PubMed:Lumichrome complexation by cyclodextrins: influence of pharmaceutical excipients.
PubMed:Lumichrome and phenyllactic acid as chemical markers of thistle (Galactites tomentosa Moench) honey.
PubMed:Absorption and emission spectroscopic characterization of lumichrome in aqueous solutions.
PubMed:Effect of substituents of alloxazine derivatives on the selectivity and affinity for adenine in AP-site-containing DNA duplexes.
PubMed:Bicomponent hydrogels of lumichrome and melamine: photoluminescence property and its dependency on pH and temperature.
PubMed:Photophysical characterisation and photo-cycle dynamics of LOV1-His domain of phototropin from Chlamydomonas reinhardtii with roseoflavin monophosphate cofactor.
PubMed:A new cytotoxic trichothecene macrolide from the endophyte Myrothecium roridum.
PubMed:Effect of divalent anions on photodegradation kinetics and pathways of riboflavin in aqueous solution.
PubMed:Absorption and emission spectroscopic characterization of BLUF protein Slr1694 from Synechocystis sp. PCC6803 with roseoflavin cofactor.
PubMed:Calculating solution redox free energies with ab initio quantum mechanical/molecular mechanical minimum free energy path method.
PubMed:Photoirradiation products of flavin derivatives, and the effects of photooxidation on guanine.
PubMed:Dodecin is the key player in flavin homeostasis of archaea.
PubMed:(1)H and (13)C NMR assignments of eight nitrogen containing compounds from Nocardia alba sp.nov (YIM 30243(T)).
PubMed:Competitive binding of small ligands to nucleobases in AP site-containing DNA duplexes.
PubMed:Effect of borate buffer on the photolysis of riboflavin in aqueous solution.
PubMed:The vitamin riboflavin and its derivative lumichrome activate the LasR bacterial quorum-sensing receptor.
PubMed:Toxicity testing of a novel riboflavin-based technology for pathogen reduction and white blood cell inactivation.
PubMed:Femtosecond pump-probe experiments on trapped flavin: optical control of dissociation.
PubMed:Nod factor [Nod Bj V (C(18:1), MeFuc)] and lumichrome enhance photosynthesis and growth of corn and soybean.
PubMed:Electron ionisation and electrospray ionisation mass spectrometric study of a series of isomeric methyl-, dimethyl- and trimethylalloxazines.
PubMed:Early interactions between legumes and rhizobia: disclosing complexity in a molecular dialogue.
PubMed:Penicidones A-C, three cytotoxic alkaloidal metabolites of an endophytic Penicillium sp.
PubMed:Oxygen uptake after electron transfer from amines, amino acids and ascorbic acid to triplet flavins in air-saturated aqueous solution.
PubMed:Nod factor enhances calcium uptake by soybean.
PubMed:Hydrogen-bonded complexes of lumichrome.
PubMed:Photolysis of formylmethylflavin in aqueous and organic solvents.
PubMed:In search of excited-state proton transfer in the lumichrome dimer in the solid state: theoretical and experimental approach.
PubMed:Photosensitizing effect of riboflavin, lumiflavin, and lumichrome on the generation of volatiles in soy milk.
PubMed:Photodynamics of the small BLUF protein BlrB from Rhodobacter sphaeroides.
PubMed:Dodecins: a family of lumichrome binding proteins.
PubMed:Chromatographic study of photolysis of aqueous cyanocobalamin solution in presence of vitamins B and C.
PubMed:Ground- and excited-state double proton transfer in lumichrome/acetic acid system: theoretical and experimental approach.
PubMed:Effects of riboflavin on the phototransformation of benzo[a]pyrene.
PubMed:Effect of light intensity and wavelengths on photodegradation reactions of riboflavin in aqueous solution.
PubMed:Identification and functional characterization of riboflavin transporter in human-derived retinoblastoma cell line (Y-79): mechanisms of cellular uptake and translocation.
PubMed:Mechanism of riboflavin uptake by cultured human retinal pigment epithelial ARPE-19 cells: possible regulation by an intracellular Ca2+-calmodulin-mediated pathway.
PubMed:Retymicin, galtamycin B, saquayamycin Z and ribofuranosyllumichrome, novel secondary metabolites from Micromonospora sp. Tü 6368. II. Structure elucidation.
PubMed:Retymicin, galtamycin B, saquayamycin Z and ribofuranosyllumichrome, novel secondary metabolites from Micromonospora sp. Tü 6368. I. Taxonomy, fermentation, isolation and biological activities.
PubMed:The rhizosphere signal molecule lumichrome alters seedling development in both legumes and cereals.
PubMed:Xylem transport and shoot accumulation of lumichrome, a newly recognized rhizobial signal, alters root respiration, stomatal conductance, leaf transpiration and photosynthetic rates in legumes and cereals.
PubMed:Effect of phosphate buffer on photodegradation reactions of riboflavin in aqueous solution.
PubMed:Separation, identification and quantification of riboflavin and its photoproducts in blood products using high-performance liquid chromatography with fluorescence detection: a method to support pathogen reduction technology.
PubMed:Pathogen reduction of buffy coat platelet concentrates using riboflavin and light: comparisons with pathogen-reduction technology-treated apheresis platelet products.
PubMed:Photolysis of riboflavin in aqueous solution: a kinetic study.
PubMed:A study of simultaneous photolysis and photoaddition reactions of riboflavin in aqueous solution.
PubMed:Kinetic mechanism and quaternary structure of Aminobacter aminovorans NADH:flavin oxidoreductase: an unusual flavin reductase with bound flavin.
PubMed:Effects of riboflavin photoproducts on microbial activity during photosensitization of atrazine transformation.
PubMed:Comparison of the voltammetric studies at mercury and glassy carbon electrodes for the interaction of lumichrome with DNA and analytical applications.
PubMed:Pathogen inactivation of blood components: current status and introduction of an approach using riboflavin as a photosensitizer.
PubMed:Photophysical properties of lumichromes in water.
PubMed:Structure of human biliverdin IXbeta reductase, an early fetal bilirubin IXbeta producing enzyme.
PubMed:The riboflavin-mediated photooxidation of doxorubicin.
PubMed:Riboflavin transport by isolated perfused rabbit renal proximal tubules.
PubMed:Proliferation of peripheral blood mononuclear cells increases riboflavin influx.
PubMed:Analysis of initial fouling process in coastal environment: effects of settlement, attachment, and metamorphosis promoters.
PubMed:The flavin coenzymes: a new class of group I intron inhibitors.
PubMed:Riboflavin uptake by human-derived colonic epithelial NCM460 cells.
PubMed:Initial-rate kinetics of the flavin reductase reaction catalysed by human biliverdin-IXbeta reductase (BVR-B).
PubMed:Identification of lumichrome as a sinorhizobium enhancer of alfalfa root respiration and shoot growth.
PubMed:Lumichrome. A larval metamorphosis-inducing substance in the ascidian Hhalocynthia roretzi.
PubMed:[Marine natural products influencing larval settlement and metamorphosis of marine sessile organisms].
PubMed:Light regime, riboflavin, and pH effects on 2,4-D photodegradation in water.
PubMed:Riboflavin transport by rabbit renal basolateral membrane vesicles.
PubMed:Riboflavin uptake by the human-derived liver cells Hep G2: mechanism and regulation.
PubMed:Radical oxidation of riboflavin.
PubMed:Riboflavin transport by rabbit renal brush border membrane vesicles.
PubMed:Is the NAD(P)H:flavin oxidoreductase from Escherichia coli a member of the ferredoxin-NADP+ reductase family?. Evidence for the catalytic role of serine 49 residue.
PubMed:The mechanism and substrate specificity of the NADPH:flavin oxidoreductase from Escherichia coli.
PubMed:Riboflavin uptake by rat liver basolateral membrane vesicles.
PubMed:Riboflavin uptake by native Xenopus laevis oocytes.
PubMed:Stereospecificity of hydride transfer and substrate specificity for FMN-containing NAD(P)H-flavin oxidoreductase from the luminescent bacterium, Vibrio fischeri ATCC 7744.
PubMed:Protective effects of riboflavin and its derivatives against ischemic reperfused damage of rat heart.
PubMed:Specificity of riboflavin molecular groups for riboflavin binding to rat small intestinal brush border membrane.
PubMed:Mechanism of riboflavine uptake by Caco-2 human intestinal epithelial cells.
PubMed:Uptake of riboflavin by intestinal basolateral membrane vesicles: a specialized carrier-mediated process.
PubMed:Mechanism of transport of riboflavin in rabbit intestinal brush border membrane vesicles.
PubMed:Oxidation of 1,1-diphenylhydrazine to N-nitrosodiphenylamine by superoxide radical in the eye.
PubMed:Separation, identification and determination of lumichrome in swine feed and kidney.
PubMed:Spectrophotometric assay of formylmethylflavin and photoproduct-lumichrome in organic solvents.
PubMed:Effect of solvent on UV and visible spectra of formylmethylflavin and photoproducts.
PubMed:Multicomponent spectrophotometric assay of riboflavine and photoproducts.
PubMed:Ultraviolet radiation-induced photodegradation and 1O2, O2-. production by riboflavin, lumichrome and lumiflavin.
PubMed:Intestinal absorption of riboflavin, studied by an in situ circulation system using radioactive analogues.
PubMed:Riboflavin status and photo-induced riboflavin binding to the proteins of the rat ocular lens.
PubMed:Possible involvement of lumichrome in the binding of storage protein to its receptor in Sarcophaga peregrina.
PubMed:Clarification and quantitation of primary (tissue) and secondary (microbial) catabolites of riboflavin that are excreted in mammalian (rat) urine.
PubMed:Photodegradation of sulfa drugs by fluorescent light.
PubMed:Variations in riboflavin binding by human plasma: identification of immunoglobulins as the major proteins responsible.
PubMed:Urinary lumichrome-level catabolites of riboflavin are due to microbial and photochemical events and not rat tissue enzymatic cleavage of the ribityl chain.
PubMed:Studies on the 4-carbon compound needed for the formation of the O-xylene ring of riboflavin.
PubMed:A metabolite of riboflavin binds to the 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) receptor.
PubMed:Reduction of lumichrome by the radical anions of CO2 and lipoamide.
PubMed:Occurrence of riboflavinyl glucoside in rat urine.
PubMed:New metabolites of riboflavin appeared in rat urine.
PubMed:Reduction, oxidation, and addition reactions between free radicals and flavins.
PubMed:Purification of phytochrome by Affi-Gel Blue chromatography; an effect of lumichrome on purified phytochrome.
PubMed:An efficient bacterial bioluminescence with reduced lumichrome.
PubMed:Lumiflavin and lumichrome transport in the central nervous system.
PubMed:Riboflavin transport in the central nervous system. Characterization and effects of drugs.
PubMed:[Operon study of riboflavin biosynthesis in Bacillus subtilis. XII. The determination of the ATP:riboflavin-5'-phosphotransferase and riboflavinsynthetase content in the cells with varying genotypes].
PubMed:15N nuclear magnetic resonance of flavins.
PubMed:Photochemical hydroxylation of 7,8-dimethylalloxazine (lumichrome)--a flash photolysis study.
PubMed:Intramolecular addition of the riboflavin side chain. Anion-catalyzed neutral photochemistry.
PubMed:An anomalous effect of the intermediate products of riboflavine photolysis on the intestinal absorption of poorly absorbed water-solbule drug in rats.
PubMed:[Operon of riboflavin synthesis in Bacillus subtilis. IX. Preparation and properties of lumiflavin- or lumichrome-resistant mutants].
PubMed:Photoconversion of riboflavin to lumichrome in plant tissues.
PubMed:Microspectrophotometry and the photoreceptor of Phycomyces I.
PubMed:The precursors of the xylene ring in riboflavine.
PubMed:Absorption spectra of riboflavin, lumiflavin, and lumichrome in organic solvents.
PubMed:Microbiological Aspects of Riboflavin: I. Introduction. II. Bacterial Oxidation of Riboflavin to Lumichrome.
 
Notes:
None found
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